Electrogenerated base (EG base) induced hydroxymethylation of the side chain of nitroalkylbenzenes with paraformaldehyde

Sigeru Torii, Yasuo Murakami, Hideo Tanaka, Koichi Okamoto

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Hydroxymethylation of nitroalkylbenzenes with paraformaldehyde was accomplished by electrolysis in a (CH2O)n-DMF-Et4NOTs-(Pt electrode) system. The reaction was found to be catalytic (0.25 faraday/mol) and dependent on the electroreduction of formaldehyde and/or nitroalkylbenzene. A variety of nitroalkylbenzenes were transformed to their corresponding mono- and/or bishydroxymethylated derivatives in good yield. The product yield and selectivity were shown to depend on the order of reagent addition, solvent, supporting electrolyte, and structure of the starting nitroalkylbenzenes. A plausible mechanism of the generation of base catalysts (EG base) in electroreductive media is discussed.

Original languageEnglish
Pages (from-to)3143-3147
Number of pages5
JournalJournal of Organic Chemistry
Issue number16
Publication statusPublished - 1986


ASJC Scopus subject areas

  • Organic Chemistry

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